Síntese e estudo físico-químico de 1,3-imidazóis 2,4,5-trissubstituídos derivados de benzocalcogenazóis

Detalhes bibliográficos
Ano de defesa: 2016
Autor(a) principal: Heck, Elisiane Frantz lattes
Orientador(a): Dornelles, Luciano lattes
Banca de defesa: Fantinel, Leonardo lattes, Dalcol, Ionara Irion lattes, Villetti, Marcos Antonio lattes
Tipo de documento: Tese
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
Programa de Pós-Graduação: Programa de Pós-Graduação em Química
Departamento: Química
País: Brasil
Palavras-chave em Português:
Imidazóis
Reação multicomponente
Benzoxazóis
Benzotiazóis
Fluorescência
Atividade antinociceptiva
Palavras-chave em Inglês:
Imidazoles
Multicomponent reaction
Benzoxazoles
Benzothiazoles
Fluorescence
Antinociceptive activity
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/17776
Resumo: In the following work, an unprecedented series of 2,4,5-trisubstituted 1,3-imidazoles were synthesized from 1,2-diketones and aryl aldehydes, targeting the union of two classes of heterocyclic rings, the imidazoles and benzocalcogenazoles in order to explore their physical, chemical and biological properties. The 1,2-diketones were obtained from a terminal arylalkyne oxidation reaction, with yields ranging from 80-95% and 84-90%, respectively, for derivatives of benzothiazoles and benzoxazoles. For the synthesis of 2,4,5-trisubstituted imidazole, used the modified Radziszewski multicomponent reaction, they are reacted where the 1,2-diketones and aryl aldehydes with ammonium acetate in acetic acid as solvent, at presence of BF3.OEt2 catalysts to obtain the imidazoles derivatives of benzoxazoles and SnCl2.2H2O for derivatives of benzothiazoles. The yields obtained for the compounds ranged from 72-98% and 68-94%, respectively. From the physico-chemical study, it was observed that the compounds fluorescence and the same varies with the substituent present in its structure. Five compounds, 2,4,5-trisubstituted imidazoles derivatives of benzoxazoles were evaluated for antinociceptive activity, and noted that one of these had a similar result to the positive control, indomethacin.
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spelling 2019-08-07T17:40:42Z2019-08-07T17:40:42Z2016-07-29http://repositorio.ufsm.br/handle/1/17776In the following work, an unprecedented series of 2,4,5-trisubstituted 1,3-imidazoles were synthesized from 1,2-diketones and aryl aldehydes, targeting the union of two classes of heterocyclic rings, the imidazoles and benzocalcogenazoles in order to explore their physical, chemical and biological properties. The 1,2-diketones were obtained from a terminal arylalkyne oxidation reaction, with yields ranging from 80-95% and 84-90%, respectively, for derivatives of benzothiazoles and benzoxazoles. For the synthesis of 2,4,5-trisubstituted imidazole, used the modified Radziszewski multicomponent reaction, they are reacted where the 1,2-diketones and aryl aldehydes with ammonium acetate in acetic acid as solvent, at presence of BF3.OEt2 catalysts to obtain the imidazoles derivatives of benzoxazoles and SnCl2.2H2O for derivatives of benzothiazoles. The yields obtained for the compounds ranged from 72-98% and 68-94%, respectively. From the physico-chemical study, it was observed that the compounds fluorescence and the same varies with the substituent present in its structure. Five compounds, 2,4,5-trisubstituted imidazoles derivatives of benzoxazoles were evaluated for antinociceptive activity, and noted that one of these had a similar result to the positive control, indomethacin.No presente trabalho, duas séries inéditas de 1,3-imidazóis 2,4,5-trissubstituidos foram sintetizados a partir de 1,2-dicetonas e arilaldeídos, com o objetivo de unir dois núcleos heterocíclicos interessantes, os 1,3-imidazóis e os benzocalcogenazóis, a fim de explorar as suas propriedades físico-químicas e biológicas. As 1,2-dicetonas foram obtidas a partir de uma reação de oxidação de arilalcinos terminais, com rendimentos que variaram de 80-95% e 84-90% respectivamente, para os derivados dos benzoxazóis e benzotiazóis. Para a síntese dos 1,3-imidazóis 2,4,5-trissubstituídos utilizou-se a reação multicomponente de Radziszewski modificada, onde reagiram-se as 1,2-dicetonas com arilaldeídos e acetato de amônio em ácido acético como solvente, na presença dos catalisadores BF3.OEt2 para obtenção dos 1,3-imidazóis derivados dos benzoxazóis e SnCl2.2H2O para os derivados dos benzotiazóis. Os rendimentos para os compostos obtidos variaram de 72-98% e 68-94%, respectivamente. A partir do estudo físico-químico realizado, observou-se que os compostos apresentam fluorescência e a mesma varia de acordo com o substituinte presente em sua estrutura. Cinco compostos, os 1,3-imidazóis-2,4,5-trissubstituídos derivados dos benzoxazóis, foram avaliados para atividade antinociceptiva, sendo observado que um destes apresentou um resultado semelhante ao controle positivo, a indometacina.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessImidazóisReação multicomponenteBenzoxazóisBenzotiazóisFluorescênciaAtividade antinociceptivaImidazolesMulticomponent reactionBenzoxazolesBenzothiazolesFluorescenceAntinociceptive activityCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese e estudo físico-químico de 1,3-imidazóis 2,4,5-trissubstituídos derivados de benzocalcogenazóisSynthesis and physico-chemical study of 2,4,5-trisubstituted imidazoles derivatives of benzocalcogenazoisinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisDornelles, Lucianohttp://lattes.cnpq.br/7629319262073140Fantinel, Leonardohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4777461U9Dalcol, Ionara Irionhttp://lattes.cnpq.br/9769548819312192Villetti, Marcos Antoniohttp://lattes.cnpq.br/8504489050993642http://lattes.cnpq.br/0684846327534219Heck, Elisiane Frantz1006000000006006b4b1c8a-fdd1-49f0-a8ce-2d891b6579b6573a509e-7583-4272-bf7b-18bc70680a54b0e1e2a5-71c6-4a3f-9161-9fa6805b8b49a40bb239-8ee1-458e-9d6a-c027ca35d1ff8437eadf-3a57-4c40-ac38-2583cb529b98reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2016_HECK_ELISIANE.pdfTES_PPGQUIMICA_2016_HECK_ELISIANE.pdfTese de Doutoradoapplication/pdf8221828http://repositorio.ufsm.br/bitstream/1/17776/1/TES_PPGQUIMICA_2016_HECK_ELISIANE.pdf417a3f47d949f9fcf03ef19fbb59fc0dMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv Síntese e estudo físico-químico de 1,3-imidazóis 2,4,5-trissubstituídos derivados de benzocalcogenazóis
dc.title.alternative.eng.fl_str_mv Synthesis and physico-chemical study of 2,4,5-trisubstituted imidazoles derivatives of benzocalcogenazois
title Síntese e estudo físico-químico de 1,3-imidazóis 2,4,5-trissubstituídos derivados de benzocalcogenazóis
spellingShingle Síntese e estudo físico-químico de 1,3-imidazóis 2,4,5-trissubstituídos derivados de benzocalcogenazóis
Heck, Elisiane Frantz
Imidazóis
Reação multicomponente
Benzoxazóis
Benzotiazóis
Fluorescência
Atividade antinociceptiva
Imidazoles
Multicomponent reaction
Benzoxazoles
Benzothiazoles
Fluorescence
Antinociceptive activity
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese e estudo físico-químico de 1,3-imidazóis 2,4,5-trissubstituídos derivados de benzocalcogenazóis
title_full Síntese e estudo físico-químico de 1,3-imidazóis 2,4,5-trissubstituídos derivados de benzocalcogenazóis
title_fullStr Síntese e estudo físico-químico de 1,3-imidazóis 2,4,5-trissubstituídos derivados de benzocalcogenazóis
title_full_unstemmed Síntese e estudo físico-químico de 1,3-imidazóis 2,4,5-trissubstituídos derivados de benzocalcogenazóis
title_sort Síntese e estudo físico-químico de 1,3-imidazóis 2,4,5-trissubstituídos derivados de benzocalcogenazóis
author Heck, Elisiane Frantz
author_facet Heck, Elisiane Frantz
author_role author
dc.contributor.advisor1.fl_str_mv Dornelles, Luciano
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/7629319262073140
dc.contributor.referee1.fl_str_mv Fantinel, Leonardo
dc.contributor.referee1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4777461U9
dc.contributor.referee2.fl_str_mv Dalcol, Ionara Irion
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/9769548819312192
dc.contributor.referee3.fl_str_mv Villetti, Marcos Antonio
dc.contributor.referee3Lattes.fl_str_mv http://lattes.cnpq.br/8504489050993642
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/0684846327534219
dc.contributor.author.fl_str_mv Heck, Elisiane Frantz
contributor_str_mv Dornelles, Luciano
Fantinel, Leonardo
Dalcol, Ionara Irion
Villetti, Marcos Antonio
dc.subject.por.fl_str_mv Imidazóis
Reação multicomponente
Benzoxazóis
Benzotiazóis
Fluorescência
Atividade antinociceptiva
topic Imidazóis
Reação multicomponente
Benzoxazóis
Benzotiazóis
Fluorescência
Atividade antinociceptiva
Imidazoles
Multicomponent reaction
Benzoxazoles
Benzothiazoles
Fluorescence
Antinociceptive activity
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Imidazoles
Multicomponent reaction
Benzoxazoles
Benzothiazoles
Fluorescence
Antinociceptive activity
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description In the following work, an unprecedented series of 2,4,5-trisubstituted 1,3-imidazoles were synthesized from 1,2-diketones and aryl aldehydes, targeting the union of two classes of heterocyclic rings, the imidazoles and benzocalcogenazoles in order to explore their physical, chemical and biological properties. The 1,2-diketones were obtained from a terminal arylalkyne oxidation reaction, with yields ranging from 80-95% and 84-90%, respectively, for derivatives of benzothiazoles and benzoxazoles. For the synthesis of 2,4,5-trisubstituted imidazole, used the modified Radziszewski multicomponent reaction, they are reacted where the 1,2-diketones and aryl aldehydes with ammonium acetate in acetic acid as solvent, at presence of BF3.OEt2 catalysts to obtain the imidazoles derivatives of benzoxazoles and SnCl2.2H2O for derivatives of benzothiazoles. The yields obtained for the compounds ranged from 72-98% and 68-94%, respectively. From the physico-chemical study, it was observed that the compounds fluorescence and the same varies with the substituent present in its structure. Five compounds, 2,4,5-trisubstituted imidazoles derivatives of benzoxazoles were evaluated for antinociceptive activity, and noted that one of these had a similar result to the positive control, indomethacin.
publishDate 2016
dc.date.issued.fl_str_mv 2016-07-29
dc.date.accessioned.fl_str_mv 2019-08-07T17:40:42Z
dc.date.available.fl_str_mv 2019-08-07T17:40:42Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/doctoralThesis
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status_str publishedVersion
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url http://repositorio.ufsm.br/handle/1/17776
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dc.rights.driver.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
dc.publisher.program.fl_str_mv Programa de Pós-Graduação em Química
dc.publisher.initials.fl_str_mv UFSM
dc.publisher.country.fl_str_mv Brasil
dc.publisher.department.fl_str_mv Química
publisher.none.fl_str_mv Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas
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